Cyclohexene oxide

Structural formula
General
Surname	Cyclohexene oxide
other names	Cyclohexane-1,2-epoxide; 7-oxa-bicyclo [4.1.0] heptane; 3,4-diepoxycyclohexane; 1,2-epoxycyclohexane;
Molecular formula	C 6 H 10 O
Brief description	colorless liquid
External identifiers / databases
EC number	206-007-7
ECHA InfoCard	100.005.462
PubChem	9246
Wikidata	Q2750068
properties
Molar mass	98.145 g mol −1
Physical state	liquid
density	0.97 g cm −3
Melting point	approx. −40 ° C
boiling point	approx. 130 ° C
Vapor pressure	12 mbar (at 20 ° C)
solubility	practically insoluble in water
safety instructions
H and P phrases	H: 226-302-311 + 331-314
	P: 261-280-305 + 351 + 338-310-309 + 310
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cyclohexene oxide is a cycloaliphatic epoxide . It can react in cationic polymerization to form poly (cyclohexene oxide) . Since cyclohexene oxide is monovalent , poly (cyclohexene oxide) is a thermoplastic .

Manufacturing

Cyclohexene oxide is produced from cyclohexene in an epoxidation process. The epoxidation can either take place in a homogeneous reaction medium by peracids or heterogeneously catalyzed (e.g. by silver with molecular oxygen):

In industrial production, the heterogeneously catalyzed production is preferred because of better atom economy , easier separation of the product and easy recycling of the (used) catalyst. A brief overview of the oxidation of cyclohexene by hydrogen peroxide is given in the literature. Recently, it was found that the catalytic oxidation by immobilized metallo - complexes represents an efficient way.

analysis

Cyclohexene oxide has been studied extensively using analytical methods. A good overview is given in the literature. A study on the polymerization of cyclohexene oxide in solution and the IR , ¹ H-NMR and MALDI-TOF spectra of the product together with the SEC chromatograms can be found in the literature.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on 1,2-epoxycyclohexane in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
↑ M. Quenard, V. Bonmarin, G. Gelbard: Epoxidation of olefins by hydrogen peroxide catalyzed by phosphonotungstic complexes. In: Tetrahedron Letters. 28, 1987, pp. 2237-2238, doi: 10.1016 / S0040-4039 (00) 96089-1 .
^ Ha Q. Pham, Maurice J. Marks: Epoxy Resins . doi : 10.1002 / 14356007.a09_547.pub2 .
↑ Siegfried Rebsdat, Dieter Mayer: Ethylene Oxide . doi : 10.1002 / 14356007.a10_117 .
↑ Spectroscopic investigation of the molybdenum active sites on Mo ^VI heterogeneous catalysts for alkene epoxidation . In: Journal of the Chemical Society, Faraday Transactions . 1995. doi : 10.1039 / FT9959103969 .
↑ VK Ambili, p Sugunan: Studies on Catalysis by Ordered Mesoporous SBA-15 material Modified with Transition Metals . Ed .: Faculty of Sciences. ( dyuthi.cusat.ac.in [accessed July 27, 2014]).
↑ Costa, Andréia A. Ghesti, Grace F. de Macedo, Julio L. Braga, Valdeilson S. Santos, Marcello M. Dias, José A. Dias, CL Sílvia: Immobilization of Fe, Mn and Co tetraphenylporphyrin complexes in MCM-41 and their catalytic activity in cyclohexene oxidation reaction by hydrogen peroxide . In: Journal of Molecular Catalysis A: Chemical . 282, No. 1-2, 2008, pp. 149-157. doi : 10.1016 / j.molcata.2007.12.024 .
↑ Xian-Tai Zhou, Hong-Bing Ji, Jian-Chang Xu, Li-Xia Pei, Le-Fu Wang, Xing-Dong Yao: Enzymatic-like mediated olefins epoxidation by molecular oxygen under mild conditions . In: Tetrahedron Letters . 48, No. 15, 2007, pp. 2691-2695. doi : 10.1016 / j.tetlet.2007.02.066 .
↑ RM Ibberson, O. Yamamuro, I. Tsukushi: The crystal structures and phase behavior of cyclohexene oxide . In: Chemical physics letters . 423, No. 4-6, 2006, pp. 454-458. doi : 10.1016 / j.cplett.2006.04.004 .
↑ Ahmed Yahiaoui, Mohammed Belbachir, Jeanne Claude Soutif, Laurent Fontaine: Synthesis and structural analyzes of poly (1,2-cyclohexene oxide) over solid acid catalyst . In: Materials Letters . 59, No. 7, 2005, pp. 759-767. doi : 10.1016 / j.matlet.2004.11.017 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on 1,2-epoxycyclohexane in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

[2] M. Quenard, V. Bonmarin, G. Gelbard: Epoxidation of olefins by hydrogen peroxide catalyzed by phosphonotungstic complexes. In: Tetrahedron Letters. 28, 1987, pp. 2237-2238, doi: 10.1016 / S0040-4039 (00) 96089-1 .

[3] Ha Q. Pham, Maurice J. Marks: Epoxy Resins . doi : 10.1002 / 14356007.a09_547.pub2 .

[4] Siegfried Rebsdat, Dieter Mayer: Ethylene Oxide . doi : 10.1002 / 14356007.a10_117 .

[5] Spectroscopic investigation of the molybdenum active sites on Mo ^VI heterogeneous catalysts for alkene epoxidation . In: Journal of the Chemical Society, Faraday Transactions . 1995. doi : 10.1039 / FT9959103969 .

[6] VK Ambili, p Sugunan: Studies on Catalysis by Ordered Mesoporous SBA-15 material Modified with Transition Metals . Ed .: Faculty of Sciences. ( dyuthi.cusat.ac.in [accessed July 27, 2014]).

[7] Costa, Andréia A. Ghesti, Grace F. de Macedo, Julio L. Braga, Valdeilson S. Santos, Marcello M. Dias, José A. Dias, CL Sílvia: Immobilization of Fe, Mn and Co tetraphenylporphyrin complexes in MCM-41 and their catalytic activity in cyclohexene oxidation reaction by hydrogen peroxide . In: Journal of Molecular Catalysis A: Chemical . 282, No. 1-2, 2008, pp. 149-157. doi : 10.1016 / j.molcata.2007.12.024 .

[8] Xian-Tai Zhou, Hong-Bing Ji, Jian-Chang Xu, Li-Xia Pei, Le-Fu Wang, Xing-Dong Yao: Enzymatic-like mediated olefins epoxidation by molecular oxygen under mild conditions . In: Tetrahedron Letters . 48, No. 15, 2007, pp. 2691-2695. doi : 10.1016 / j.tetlet.2007.02.066 .

[9] RM Ibberson, O. Yamamuro, I. Tsukushi: The crystal structures and phase behavior of cyclohexene oxide . In: Chemical physics letters . 423, No. 4-6, 2006, pp. 454-458. doi : 10.1016 / j.cplett.2006.04.004 .

[10] Ahmed Yahiaoui, Mohammed Belbachir, Jeanne Claude Soutif, Laurent Fontaine: Synthesis and structural analyzes of poly (1,2-cyclohexene oxide) over solid acid catalyst . In: Materials Letters . 59, No. 7, 2005, pp. 759-767. doi : 10.1016 / j.matlet.2004.11.017 .